2 ¼ cups all purpose flour
¾ cup cocoa powder
1 tsp baking powder
½ tsp baking soda
½ tsp salt
1 stick unsalted butter, room temperature
½ cup Crisco
½ cup packed brown sugar
1 cup granulated sugar
2 large eggs
2 tsp vanilla extract
½ oz red food coloring (about ½ a bottle)
1 cup buttermilk (low-fat is fine)
Cream Cheese Icing (recipe below)
1 can cherry pie filling
Position rack to the center of the oven and preheat to 350 degrees. Line 2 baking sheets with parchment paper.
Sift together flour, cocoa, baking powder, baking soda, and salt into a medium bowl.
In the bowl of an electric mixer with a paddle attachment, beat together the butter, Crisco, and both sugars on low until combined. Increase the speed to medium and beat for 5 more minutes until fluffy. Lower the speed and add the eggs one at a time. Add the vanilla and food coloring until combined. Then beat all contents on medium for another 30 seconds.
With mixer on low, alternate adding dry ingredients and buttermilk beginning and ending with the dry ingredients. Stop mixing when completely combined, but do not over mix.
Using a spoon, drop tablespoon sized dollops of the batter on the lined baking sheets, spacing them about 2 inches from one another. Bake on sheet at a time for 10 minutes, or until the cakes spring back when lightly pressed. Allow to sit on the pan for 5 minutes before transferring to cooling racks to cool completely.
After all of the cakes have cooled, pipe a circle of the cream cheese icing on a whoopie pie cake, leaving a little hollow space in the center. Take one or two whole cherries from the pie filling and drop into that hole. Top with another whoopie pie. Repeat with remaining cakes. You will have enough to make approximately 22 – 24 whoopie pies.
Cream Cheese Icing
4 oz cream cheese, room temperature
4 Tbsp unsalted butter, room temperature
3 ½ cups confectioners sugar (16 oz box)
1 tsp vanilla
2-4 Tbsp milk
In the bowl of an electric mixer fitted with a paddle attachment, cream together the cream cheese and butter on medium speed. Add the sugar and beat on low until combined. Add the vanilla and a tablespoon of milk and beat until creamy and smooth for about 4 minutes. Add a tablespoon or two of the milk, if needed, to loosen up the icing enough to pipe and combine on medium.